Tributylstannane → HCID 20061023, compound

HRID 1085149Notes

Reaction equation

HRID 1085149 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=2)[C:5]([CH3:15])=[N:4][C:3]=1I.C([SnH](CCCC)CCCC)CCC.[F-].[K+].C1C[O:35][CH2:34]C1>>[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=2)[C:5]([CH3:15])=[N:4][C:3]=1[CH:34]=[O:35]

Participants

5

Reactant 4

HCID 5948TributylstannaneHCID 8028Tetrahydrofuran2×HCID 522689Potassium FluorideHCID 20060989HCID 20060989, compound

Product 1

HCID 20061023HCID 20061023, compound

Conditions

Temperature
50 °C

Procedure

A solution of the product from (b) (1.03 g, 3 mmol) and tetrakis (triphenylphosphine)palladium (0.3 g) in THF (70 ml) was installed under an atmosphere of carbon monoxide and heated to 50° C. Tributyltin hydride (0.96 g, 3.3 mmol) in THF (40 ml) was instilled by motor-driven syringe over 4.5 hours. After an additional 0.5 hours the mixture was stirred with 100 ml of 10% potassium fluoride solution for 15 minutes, then extracted twice with dichloromethane. The organic layers were dried over magnesium sulphate and evaporated to an orange solid.

Workup

  1. extractionextracted twice with dichloromethane
  2. dry with materialThe organic layers were dried over magnesium sulphate
  3. customevaporated to an orange solid

Sources & evidence

ORD record
ord-8515b0802c154cb3bfff6ca4b2bbdeb1
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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